N-(8-Quinolyl)-o-phenyl­enedi­amine

The crystal packing of the title compound, C₁₅H₁₃N₃, is determined by intermolecular N—H...N interactions, resulting in parallel rows of mol­ecules along [100].

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.107
• Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.30
           From the CIF: _reflns_number_total               1584
           Count of symmetry unique reflns         1585
           Completeness (_total/calc)             99.94%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SMART; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N-(8-Quinolyl)-o-phenylenediamine

Crystal data

C15H13N3	Dx = 1.299 Mg m^−3
Mr = 235.28	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 1682 reflections
a = 10.7227 (13) Å	θ = 2.6–23.2°
b = 11.0789 (13) Å	µ = 0.08 mm^−1
c = 10.1268 (12) Å	T = 120 K
V = 1203.0 (2) Å^3	Plate, colorless
Z = 4	0.50 × 0.45 × 0.02 mm
F(000) = 496

Data collection

Bruker SMART CCD area-detector diffractometer	1584 independent reflections
Radiation source: sealed tube	1409 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
φ and ω scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −8→14
Tmin = 0.941, Tmax = 0.989	k = −14→13
7244 measured reflections	l = −12→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: difference Fourier map
wR(F^2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0655P)^2] where P = (Fo^2 + 2Fc^2)/3
1584 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.28 e Å^−3
1 restraint	Δρmin = −0.20 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	−0.0321 (2)	0.4222 (2)	0.5373 (3)	0.0371 (5)
H1A	−0.002 (3)	0.472 (3)	0.480 (4)	0.042 (6)*
H1B	−0.073 (3)	0.354 (2)	0.495 (3)	0.042 (6)*
N2	0.16621 (17)	0.57715 (15)	0.6004 (2)	0.0251 (4)
H2	0.237 (3)	0.588 (2)	0.577 (4)	0.049 (9)*
N3	0.26133 (17)	0.77620 (15)	0.4798 (2)	0.0269 (4)
C1	0.0414 (2)	0.39785 (17)	0.6461 (2)	0.0264 (5)
C2	0.0178 (2)	0.2981 (2)	0.7281 (3)	0.0339 (6)
H2A	−0.0485	0.2446	0.7071	0.041*
C3	0.0897 (2)	0.2768 (2)	0.8384 (3)	0.0372 (6)
H3A	0.0725	0.2084	0.8919	0.045*
C4	0.1867 (2)	0.3534 (2)	0.8727 (3)	0.0380 (6)
H4A	0.2363	0.3379	0.9486	0.046*
C5	0.2094 (2)	0.4526 (2)	0.7940 (2)	0.0301 (5)
H5A	0.2750	0.5062	0.8171	0.036*
C6	0.13889 (19)	0.47598 (17)	0.6822 (2)	0.0232 (4)
C7	0.10372 (19)	0.68568 (17)	0.6152 (2)	0.0230 (4)
C8	−0.0067 (2)	0.69593 (19)	0.6842 (2)	0.0261 (5)
H8A	−0.0411	0.6269	0.7262	0.031*
C9	−0.0691 (2)	0.80762 (19)	0.6931 (2)	0.0297 (5)
H9A	−0.1456	0.8122	0.7400	0.036*
C10	−0.0220 (2)	0.90953 (19)	0.6356 (2)	0.0296 (5)
H10A	−0.0639	0.9846	0.6450	0.036*
C11	0.0899 (2)	0.90214 (18)	0.5619 (2)	0.0268 (5)
C12	0.1412 (2)	1.00072 (19)	0.4920 (3)	0.0330 (6)
H12A	0.1033	1.0781	0.4975	0.040*
C13	0.2452 (3)	0.98452 (19)	0.4167 (3)	0.0362 (6)
H13A	0.2784	1.0495	0.3666	0.043*
C14	0.3026 (2)	0.8707 (2)	0.4141 (3)	0.0323 (5)
H14A	0.3756	0.8612	0.3618	0.039*
C15	0.15355 (19)	0.79004 (17)	0.5516 (2)	0.0227 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0339 (11)	0.0359 (10)	0.0415 (12)	−0.0089 (9)	−0.0070 (10)	0.0051 (10)
N2	0.0204 (9)	0.0202 (8)	0.0349 (11)	0.0004 (7)	0.0074 (8)	0.0036 (7)
N3	0.0225 (9)	0.0251 (8)	0.0332 (11)	−0.0031 (7)	−0.0002 (8)	0.0038 (8)
C1	0.0214 (10)	0.0218 (9)	0.0361 (12)	0.0041 (8)	0.0045 (9)	0.0003 (9)
C2	0.0270 (12)	0.0244 (10)	0.0504 (16)	−0.0003 (8)	0.0125 (11)	0.0048 (11)
C3	0.0396 (14)	0.0299 (11)	0.0420 (14)	0.0148 (10)	0.0169 (12)	0.0141 (11)
C4	0.0389 (14)	0.0429 (13)	0.0321 (14)	0.0161 (11)	0.0056 (11)	0.0079 (11)
C5	0.0274 (11)	0.0322 (11)	0.0307 (12)	0.0055 (9)	0.0025 (10)	−0.0022 (10)
C6	0.0220 (10)	0.0194 (8)	0.0282 (11)	0.0052 (7)	0.0076 (9)	0.0026 (9)
C7	0.0230 (10)	0.0213 (9)	0.0247 (11)	−0.0007 (8)	−0.0015 (8)	−0.0011 (8)
C8	0.0252 (11)	0.0253 (9)	0.0277 (11)	0.0003 (8)	0.0031 (9)	0.0004 (9)
C9	0.0264 (11)	0.0330 (11)	0.0296 (11)	0.0054 (8)	0.0024 (9)	−0.0034 (10)
C10	0.0309 (12)	0.0241 (10)	0.0338 (13)	0.0080 (8)	−0.0041 (10)	−0.0038 (9)
C11	0.0268 (11)	0.0234 (9)	0.0302 (12)	0.0002 (8)	−0.0080 (9)	−0.0009 (9)
C12	0.0330 (12)	0.0228 (10)	0.0433 (15)	−0.0013 (9)	−0.0112 (11)	0.0045 (10)
C13	0.0340 (12)	0.0289 (10)	0.0456 (16)	−0.0095 (10)	−0.0076 (12)	0.0146 (11)
C14	0.0256 (11)	0.0337 (12)	0.0376 (13)	−0.0051 (9)	0.0003 (10)	0.0075 (10)
C15	0.0216 (10)	0.0220 (9)	0.0245 (10)	−0.0020 (8)	−0.0040 (8)	0.0019 (8)

Geometric parameters (Å, º)

N1—C1	1.381 (3)	C5—H5A	0.9500
N1—H1A	0.86 (3)	C7—C8	1.379 (3)
N1—H1B	0.97 (3)	C7—C15	1.427 (3)
N2—C7	1.385 (2)	C8—C9	1.410 (3)
N2—C6	1.424 (3)	C8—H8A	0.9500
N2—H2	0.81 (4)	C9—C10	1.367 (3)
N3—C14	1.317 (3)	C9—H9A	0.9500
N3—C15	1.374 (3)	C10—C11	1.415 (3)
C1—C6	1.406 (3)	C10—H10A	0.9500
C1—C2	1.405 (3)	C11—C12	1.413 (3)
C2—C3	1.377 (4)	C11—C15	1.421 (3)
C2—H2A	0.9500	C12—C13	1.363 (4)
C3—C4	1.387 (4)	C12—H12A	0.9500
C3—H3A	0.9500	C13—C14	1.404 (3)
C4—C5	1.379 (3)	C13—H13A	0.9500
C4—H4A	0.9500	C14—H14A	0.9500
C5—C6	1.387 (3)
C1—N1—H1A	116 (2)	C8—C7—C15	118.90 (18)
C1—N1—H1B	116.7 (17)	N2—C7—C15	118.24 (18)
H1A—N1—H1B	112 (3)	C7—C8—C9	120.8 (2)
C7—N2—C6	121.40 (18)	C7—C8—H8A	119.6
C7—N2—H2	111.2 (19)	C9—C8—H8A	119.6
C6—N2—H2	119 (2)	C10—C9—C8	121.5 (2)
C14—N3—C15	117.49 (18)	C10—C9—H9A	119.3
N1—C1—C6	120.7 (2)	C8—C9—H9A	119.3
N1—C1—C2	121.5 (2)	C9—C10—C11	119.35 (19)
C6—C1—C2	117.7 (2)	C9—C10—H10A	120.3
C3—C2—C1	120.9 (2)	C11—C10—H10A	120.3
C3—C2—H2A	119.5	C12—C11—C10	123.3 (2)
C1—C2—H2A	119.5	C12—C11—C15	116.9 (2)
C2—C3—C4	121.2 (2)	C10—C11—C15	119.76 (19)
C2—C3—H3A	119.4	C13—C12—C11	119.8 (2)
C4—C3—H3A	119.4	C13—C12—H12A	120.1
C5—C4—C3	118.4 (2)	C11—C12—H12A	120.1
C5—C4—H4A	120.8	C12—C13—C14	119.2 (2)
C3—C4—H4A	120.8	C12—C13—H13A	120.4
C4—C5—C6	121.7 (2)	C14—C13—H13A	120.4
C4—C5—H5A	119.2	N3—C14—C13	123.8 (2)
C6—C5—H5A	119.2	N3—C14—H14A	118.1
C5—C6—C1	120.2 (2)	C13—C14—H14A	118.1
C5—C6—N2	120.7 (2)	N3—C15—C11	122.70 (18)
C1—C6—N2	119.1 (2)	N3—C15—C7	117.61 (17)
C8—C7—N2	122.81 (18)	C11—C15—C7	119.68 (19)
N1—C1—C2—C3	−178.2 (2)	C8—C9—C10—C11	2.1 (4)
C6—C1—C2—C3	−1.2 (3)	C9—C10—C11—C12	175.7 (2)
C1—C2—C3—C4	0.5 (4)	C9—C10—C11—C15	−1.7 (3)
C2—C3—C4—C5	0.5 (3)	C10—C11—C12—C13	−176.0 (2)
C3—C4—C5—C6	−0.7 (3)	C15—C11—C12—C13	1.6 (3)
C4—C5—C6—C1	0.0 (3)	C11—C12—C13—C14	−2.5 (4)
C4—C5—C6—N2	−178.3 (2)	C15—N3—C14—C13	2.0 (4)
N1—C1—C6—C5	177.9 (2)	C12—C13—C14—N3	0.7 (4)
C2—C1—C6—C5	1.0 (3)	C14—N3—C15—C11	−3.0 (3)
N1—C1—C6—N2	−3.8 (3)	C14—N3—C15—C7	175.6 (2)
C2—C1—C6—N2	179.25 (19)	C12—C11—C15—N3	1.2 (3)
C7—N2—C6—C5	−95.6 (2)	C10—C11—C15—N3	178.9 (2)
C7—N2—C6—C1	86.1 (3)	C12—C11—C15—C7	−177.4 (2)
C6—N2—C7—C8	−16.3 (3)	C10—C11—C15—C7	0.3 (3)
C6—N2—C7—C15	166.3 (2)	C8—C7—C15—N3	−177.8 (2)
N2—C7—C8—C9	−177.9 (2)	N2—C7—C15—N3	−0.3 (3)
C15—C7—C8—C9	−0.6 (3)	C8—C7—C15—C11	0.9 (3)
C7—C8—C9—C10	−0.9 (4)	N2—C7—C15—C11	178.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2	0.86 (3)	2.47 (3)	2.806 (3)	104 (3)
N2—H2···N3	0.81 (4)	2.32 (3)	2.719 (2)	111 (2)
N1—H1B···N3^i	0.97 (3)	2.29 (3)	3.175 (3)	150 (2)
N2—H2···N1^ii	0.81 (4)	2.51 (4)	3.298 (3)	166 (3)

Symmetry codes: (i) x−1/2, −y+1, z; (ii) x+1/2, −y+1, z.